His wife, Leona Helmsley — notoriously called the "Queen of Mean" — was convicted in 1989 on federal charges of tax evasion in a celebrated trial. Harry had been indicted along with Leona, but it was determined that he was far too ill physically to stand trial and too weak mentally to be capable of assisting his attorneys in his own defense, one of the legal standards which allows crimes to go unprosecuted on the grounds of mental defect of the defendant.

Early career

He attended Evander Childs High School in The Bronx. He did not go to college. At age 16, he began learning the real estate business, and started working for Dwight Veerhis & Perry, where he rose from an office boy (for $12 a week) to broker to partner. He eventually purchased the firm in 1938, renaming it Dwight Voorhis & Helmsley.

Also in 1938, he married Eve Ella Sherpick Green, a widow.

In 1955, he acquired business competitor Spear & Company, which became Helmsley-Spear and expanded his holdings in lower Manhattan. He purchased real estate firm Brown Harris Stevens, which brought him into rental and cooperative apartment sales and management; it was also where he hired Leona Roberts in 1970 as senior vice president.